Condensation products of the anthracene series and process of making same.



UNITED STATES PATENT OFFICE.

ALBRECHT SCHMIDT, OF HtjCHST-ON-THE-MAIN, AND GEORG KRANZLEIN, OF SIND- LINGEN, NEAR HtjCHST-ON-THE-MAIN. GERMANY, ASSIGNORS TO FARBWERKE VORM. MEISTER LUCIUS & BRUNING, OF HCiCHST-ON-THE-MAIN, GERMANY, A COR- PORATION OF GERMANY.

CONDENSATION PRODUCTS OF THE ANTHRACENE SERIES AND PROCESS OF MAKING Patented Feb. 11, 1913.

SAME.

1 052,520, Specification of Letters Patent.

No Drawing. Application filed March 30, 1912.

Serial No. 687,451.

To all whom it may concern:

Be it known that. we, Auuuccirr SCHMIDT, Ph. D., chemist, and Gnono Kaftnztmn, Ph. D., chemist, citizens of the Empire of Germany, residing atlItichst-on-the-Main and Sindlingen, near llochst-on-the-Main, Germany, respectively. have invented certain new and useful Improvements in Condensation Products of the Anthracene Series and Processes of Making Same, of which the following is a specification.

\Ve have found that the quinones (under which term we comprise qmnone itself and its substitution products, such as halogen quinone, chloraml or the like), when combined with anthranols (under which term we comprise anthranol itself and its substitution products, such as halogen anthranols, ete.), form condensation products which can be used as vat dyestuffs and as parent products for the same.

The following exan'iples illustrate our inrention:

I. 18 kg. of anthranol are heated to boil ing for some hours with 11 kg. of quinone in kg. of nitrobenzene, whereby, in conscquence of the reaction which sets in, water is split oil, the liquid assuming an intense bluish green coloration. The oxygen re quircd for the reaction may be derived from the air, or it may be produced by the cooperation of the quinono or the nitrobenzenc. Tn any case oxidizing agents (such for instance as an excess of quinone, nitrohydrocarbons, etc.) promote the reaction. After cooling, the mass is filtered, washed with hot alcohol and dried. The dyestutl' thus obtained forms crystals of a metallic luster, which gives a reddish-violet vat, from which cotton is dyed blue tints which are not destroyed by a solution of chlorid of lime.

In the place of anthranol there may be employed substituted anthranols, whereby (litl'erences ot shades may be obtained, as will be seen by the tabular statement hereafter to be found.

TI. 19.?) kg. of anthranol are boiled for some days on the, reflux apparatus with 2 tkg. of ehloranil in 300 kg. of xylene. The liquid assumes an intense green color with formation of hyt'lrochloric aeid,while slowly separating the dyestutl'. The latter, after cooling, is filtered off, washed with alcohol and dried. line powder is obtained, iving a bluish violet vat which dyes cotton clear green tints of excellent fastness to washing and resisting well the action of chlorin. The formation of thc'dyestutf may be facilitated by an agent neutralizing hydrochloric acid, for instance anhydrous sodium acetate, or a. catalytic agent, for instance copper chloi'id.

it the condensation is etlectcd in a medium ot a higher boiling point, for instance in uitrobenzene, there is obtained a blue dyestutl' after extraction of the product of the reaction by means of hot alcohol, which (lyestutl very much resembles that obtained according to Example l, as regards its tinetorial properties. in an analogous manner, by using other anthrnnols there are obtained ditl'erent reaction products, according as they are condensed with chloranil at a higher or at a lower temperature. Thus, for instance, the product obtainable in the same way according to Example IT., by the reaction of ti-aminoanthranol with chlorauil in xylene, constitutes a dycstutt dyeing cotton olive-green tints, whereas that obtained when using nitrobenzene instead of xylene dyes bluislrgray tints.

The following tabular statement refers Thus a grecnislrblack crystaltit) to Example I and gives the tints obtainable by the various dyestufi's:

Solution Dyelngs n eoncen- Co or 0 on cotton D) trated eulthe vet. utter turlo acid. soaplug.

(1) Anthrauol+quinonc Violet-red Violetrred Blue.

(2) Anthrnnol from wchlor- Brown.... Brownlsh Gray.

authraquinono'i-quluoue. red.

(8) Anthmnol from fi-chlor- Vlolet- Reddlsh- Gray.

authmqulnone+qulnone. brown. brown.

(4) p-methylantiiranol +qut- D n l l Brownisn Green.

none. brown. violet.

(6) Chlornaphthauthrauol+ Olive yel- Browuish- Brown quluone. 10W. orange.

(0) Anthrauol ot the fill-di- Brownlsh Vlolet.... iilulshanthraquluonyluren-i-qulgray. none.

(7) Dlanthranol+quinone.... Brownlsh. Violet.... Blue.

(8) Anthranol chloranii in Fuchsia Violet, Blue.

nitrobeulcne. red.

(9) Anthrnnol chlornnll in Brownie! Bl ulsh Green.

xylene. rod. violet.

(10) fl-amluonnthranOl-i- Oliveyel- ()live..... Gm ish cnloraulliu xylene. low. 01 ve,

Having now described our invention, what we claim is:

1. The process of manufacturing condensation products of the anthracene series, which consists in condensing anthranols with quinoncs.

2. The process of manufacturing condensation products of the anthracene series, which consists in combininganthranols with quinones in presence of a suitable medium.

3. The process of manufacturing condensation products of the anthracenc series, which consists in combining anthranols with quinones in presence of a suitable medium and an agent neutralizing hydrochloric acid.

4. As new articles of manufacture, the condensation products of an anthranol with a quinone, being crystalline owders, in soluble in dilute acids and al (alis, soluble in concentrated sulfuric acid to yellow, brown to red tint-s, yielding when treated with alkaline reducing agents, brown, red to violet vats which (lye cotton, after soaping, blue, green to olive-gray tints of excellent fastncss.

As a new article of manufacture, the condensation product of anthranol and chloranil, being a greenish-black crystalline powder, solublein concentrated sulfuric acid with a brownish-red color and which dyes cotton from the hydrosulfite vat, showing a bluish-violet color, after soaping, greenish tints of excellent fastness to washing and bowkin" and resisting very well the action of chlorin.

In testimony whereof, we aiiix our signatures in presence of two witnesses.

ALBRECHT SCHMIDT. GEORG KRIXNZLEIN.

\Vitnesscs:

JEAN GnUNo, CARL GRUND.

Copies of this patent may be obtained (or five cents each, by addressing the Commissioner of Patents, Washington, D. C. 

